Itaconic acid di:ester prodn. from phosphono-succinate and aldehyde - useful as UV absorbers, monomers and dye intermediates

摘要

Prodn. of diesters of formula X-OH:C(COOR)-CH2-COOR (I) comprises reacting a phosphonosuccinate (YO)2P(O)-CH(COOR)-CH2COOR (II) with aldehyde X-CHO (III) in aq. and/or alcohol medium in presence of alkali(ne earth)hydroxides, alkali carbonates, alkaline earth oxides or tert. amines. (R is opt. substd. alk(en)yl, aralkyl, cycloalkyl or aryl; X is H, heteroaryl, or as R; Y is lower alkyl). (I) are new where X is opt. substd. 6-20C (ar)alkyl, cycloalkyl or naphthyl; substd. phenyl, or 1-6C alkyl. (I) where X is aryl are useful as UV absorbers and dye intermediates (e.g. cyclisation, followed by saponification and decarboxylation gives naphthols) and those where X is hydrogen are monomers for prodn. of high polymers (paints, coatings, binders or plastics). The method is simpler than the known process which uses special bases (e.g. NaH) in anhydrous media. (I) are obtd. in good yield and excellent purity.